Holiday Homes in Southern Oregon

Find and book unique holiday homes on Airbnb

Top-rated Holiday Homes in Southern Oregon

Guests agree: These holiday homes are highly rated for location, cleanliness and more.

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Top Guest favourite
A modern kitchen features white cabinetry and stainless steel appliances. A wooden dining table with four chairs is positioned in the foreground, while a small vase of flowers adds a touch of color. Large sliding glass doors open to a deck, inviting natural light into the space.
Holiday home in Bend
4.95 out of 5 average rating, 80 reviews

Dog friendly home, with A/C, near Deschutes River

Cozy home nestled in a grove of Aspen trees on a 1 acre lot. Sunriver Village, fishing, hiking, golfing, & more all within 10 min. Mt.Bachelor is a 30 min. drive. The master bedroom has a king size bed and it’s own bathroom. The other 2 bedrooms have queen beds. The couch in the living room has a queen pull out bed. While drinking your morning coffee or eating your evening dinner keep an eye out for the majestic wildlife. Peaceful quiet neighborhood. Pets allowed. Pet fee $15 per night per pet

Top Guest favourite
A newly constructed two-story building features a spacious exterior with a combination of wood and stone siding. The property boasts two large garage doors and an expansive gravel driveway. Surrounding pine trees provide a natural backdrop, creating a serene outdoor environment.
Holiday home in Crescent Lake
4.97 out of 5 average rating, 35 reviews

Newly Constructed Apartment in Prime Location!

Turnkey, newly constructed 1BR/1BA that sleeps 4. Includes primary BD w/a king bed, American Leather queen size sleeper sofa in living room, full BA w/tub & shower, full kitchen w/dishwasher, oven, microwave, coffee maker and more. Additional amenities include washer/dryer, Wi-Fi, TV, 40’ covered RV parking, outdoor balcony, & fire pit. Great location in Diamond Peaks. Enjoy easy access to lakes, hiking, biking, and snowmobile trails, Willamette Pass Ski Area, the PCT, & easy access to Hwy 58.

Top Guest favourite
A well-maintained hot tub is positioned on a wooden deck, surrounded by shaded areas and greenery. Outdoor furniture includes a table with two chairs, complemented by a large red umbrella providing shade. A fence offers privacy, enhancing the tranquil backyard setting.
Holiday home in Eugene
4.99 out of 5 average rating, 115 reviews

Cheerful 2-Bedroom, 2 Bath Home with Hot Tub

2 BR and 2 Bath, Newly Remodeled Home w/Hot Tub Autzen Stadium-Hayward Field-University of Oregon are approx.15 min and 5 miles away Eugene Airport is 10 min The Cheerful Cottage is a charming, sparkly clean home with hardwood floors; fully stocked kitchen; tasteful and comfortable furnishings and art! The hot tub is well maintained and located directly behind the cottage by the deck for easy access. Across the street is a lovely park and recreation center with an indoor pool and sauna.

Top Guest favourite
Holiday home in Coos Bay
5 out of 5 average rating, 90 reviews

Oceanfront Home, Lighthouse, Beach Access, Sunsets

This private 1 BR/1BA apartment is the first floor of a 3-story house perched directly above the crashing Pacific Ocean waves. Only 200 feet away, there is private access to Lighthouse Beach, a ½ mile sandy beach between rocky headlands from the north or south, it is the closest thing to a private beach in Oregon. Enjoy amazing views of Gregory Point, the historic Cape Arago lighthouse on Chiefs' Island, and Lighthouse Beach from every room in this spectacularly located one bedroom apartment.

Guest favourite
A two-story vacation house is surrounded by lush greenery, showcasing a blend of wood and modern architectural features. The upper level includes multiple windows allowing natural light. A covered area beneath offers a shaded outdoor space, while wooden fencing defines the property.
Holiday home in Eugene
4.91 out of 5 average rating, 233 reviews

Mood in Wood with private serenity in the city

Nestled within the serene embrace of a picturesque landscape, Mood in Wood is a charming vacation house that promises a harmonious blend of modern luxury and natural beauty and offers a perfect escape from the bustling city life. Built by an artist and craftsman, the house has private entrance, nice open view, fully equipped kitchen, washer/dryer, double-bed futon(2 guests), WiFi, TV, close to scenic hiking trails, 20 min to winery farm to enjoy beautiful scenery of Willamette Valley.

Superhost
The outdoor area showcases a spacious heated swimming pool surrounded by landscaped gardens. Adjacent to the pool, a hot tub is framed by natural stone and lush greenery. Sun loungers are positioned around the pool, offering a relaxing atmosphere amidst tall trees.
Holiday home in Bend
4.85 out of 5 average rating, 26 reviews

Beautiful Resort Home- Pools, Hot Tub, Hiking, Ski

This amazing resort is the ideal getaway. This is a 1 bed 1 bath with a murphy bed and sofa bed and a single person fold out bed. 3 heated pools, hot tubs, fitness center, sauna, volleyball, and an onsite restaurant and bar. Just minutes to downtown Bend where you'll find a large array of shops, breweries, restaurants, and dozens of outdoor activities. This is the closest lodging you can get to Mt Bachelor. Just a short walk to the Deschutes River for river rafting, and paddle board.

Top Guest favourite
A wooden home is featured with a large covered deck supported by exposed beams. The deck includes a seating area and a barbecue grill, providing an outdoor space for relaxation. Surrounding pine trees and a grassy area complete the natural setting.
Holiday home in Chiloquin
4.98 out of 5 average rating, 41 reviews

Running W Ranch home on the Sprague River.

4 bedroom, 2.5 bath on a 460 acre working cattle ranch. 3 miles of the Sprague River. Beautiful decorated home overlooking the Sprague River. Our home has a open and spacious layout with a large covered deck to enjoy the view. Seating and a Gas BBQ. Room to roam. Ten miles out of the town of Chiloquin, Or. with abundance of relaxation, fishing and hunting in the area. Property is 18 miles from the Yamsi Ranch with guided fly fishing and 40 miles from beautiful Crater Lake.

Guest favourite
The exterior of a single-story home is featured, characterized by brown siding and a peaked roof. A wooden fence surrounds the front yard, and an American flag is displayed near the entrance. Soft evening light casts a warm glow over the inviting porch area.
Holiday home in Reedsport
4.94 out of 5 average rating, 115 reviews

Coastal Shenanigans!

This home is right in the middle of everything to do on the coast. Whether it's fishing the Umpqua river or the ocean, riding the dunes or shopping old town Florence. It's all 10- 30 minutes away. Go for a sunset walk on the beach! There is a nice little coffee shop close and some very good restaurants close by. There is free parking on the premises and on the street. Our driveway is 38' L x 20' W. If you are a boater, we have towels in the garage to wipe your boat off.

Top Guest favourite
Holiday home in Sunriver
4.97 out of 5 average rating, 62 reviews

4 Sunrise Way: The Best of Sunriver

Open & beautiful home, hot tub, bikes, large deck with BBQ, 10 SHARC passes, ping pong, foosball, EV charger: everything you want in Sunriver! Edge of Sunriver, easy access to Bend and Lava lands. Lots of bikes for everyone (including tag along and trailer for younger kids), tennis/pickleball rackets, tubes for the river or snow, and family games. Perfect for family vacation! Absolutely no smoking or animals on site due to allergies/asthma in host children.

Superhost
A wooden deck is visible, featuring Adirondack chairs arranged around rustic stumps. The deck leads to a modern lodge set against a backdrop of dense greenery. Soft lighting fixtures are mounted on posts, enhancing the inviting entrance of the lodge.
Holiday home in Days Creek
4.91 out of 5 average rating, 152 reviews

The Lookout •Complimentary Farm Breakfast

⸻ The Lookout is a cozy cedar-lined studio with mountain and forest views. It features a full bathroom, kitchenette with essentials, and a comfy futon that folds out to sleep 2–4 guests. We provide a continental breakfast for your first morning: fruit, yogurt, oatmeal, croissants, and coffee. Set on a peaceful, chemical-free mountain ranch with pure spring water, you’ll enjoy stargazing, fresh air, privacy, and access to trails, creeks, and wild herbal plants.

Guest favourite
An indoor heated pool features inviting blue water and gently sloping steps. The surrounding space includes large windows allowing natural light, and two orange chairs are situated nearby for relaxation. Soft lighting enhances the area, creating a calm and welcoming environment.
Holiday home in Roseburg
4.98 out of 5 average rating, 107 reviews

Bar Run Golf House With pool

Bring the whole family to this great place with lots of room for fun. Indoor heated pool for year round swimming, hot tub on the deck with great views, large TV’s for watching the game, and just a short walk or golf cart ride to the newly opened Bar Run Golf and RV Resort. Surrounded by Umpqua valleys beautiful wine country. There is truly something here for everyone.**For parties or events you need permission first and there maybe an added charge**

Superhost
Holiday home in North Bend
4.78 out of 5 average rating, 78 reviews

Quiet coastal lifestyle | Convenient Location

Enjoy a quiet coastal lifestyle in a convenient Coos Bay–North Bend location near beaches, Oregon Dunes, dining, shops, Hwy 101, fishing, golf, and local attractions. Features include fast WiFi, easy self check-in/out, a full kitchen, ample parking, comfortable living space, and all upgraded memory foam mattresses.Great for work trips, family visits, dune adventures, road trips, and longer stays. Monthly discounts available.

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